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Buying in Colombia or Chile would be the go. Both for the starting destination (North to south and vice versa). Depends what kind of money you have to spend. I would highly recommend a small bike vs a big bike. I had a big bike at one point and it nearly killed me financially and physically.
Now I've got an XR150L in Peru on Colombian plates and I'll be heading north again in July. If you've got the money I'd recommend new, you won't lose that much money on resale even with 50k kms on it because prices of used bikes stay pretty high in south America.
If I were to do it all again I'd buy another xr150l or Xr190 (even better bike but $1k more) from Colvyn y Colvyn in Santiago Chile. I'd stay at casa de matte and ask very nicely for some help getting my RUT (requirement for buying a bike in Chile, very easy).
Most important bit of advise I would give you either way is learn as much Spanish as you can. It's not like SEA where it's near impossible to learn the languages without hard study for years in each county. Make the effort to learn as much as you can and you'll get rewarded for it.
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